You Shouldn’t Rush Your Sales Onboarding Process

Give your reps time to experiment and make mistakes.

Written by Brian Nordli
Published on Mar. 09, 2022
You Shouldn’t Rush Your Sales Onboarding Process

Most sales onboarding programs follow a similar pattern. Start with an overview of the company and product, then delve into the sales process, followed by testing new hires’ skills in mock demos and discovery calls, and finally, approving them to start selling. 

Despite the uniformity, onboarding remains one of the biggest bottlenecks for sales leaders today. Just 38 percent of sales organizations feel their onboarding programs are effective, according to a joint report from the Sales Management Association and workplace training app Qstream. The challenge has only grown as sales teams navigate remote training and higher rates of turnover.

3 Sales Onboarding Tips

  • Foster relationship-building opportunities.
  • Break up lectures with hands-on experience.
  • Set realistic goals and let your reps make mistakes.     

As a sales leader, Amyra Rand said there’s often pressure to speed up the training process so that a representative can start generating revenue as soon as possible. But her secret to building an effective new hire pipeline is simple — resist the pressure and don’t rush the training. 

“Every time you have a new hire, nobody wants to put them through a new hire class. It takes a lot of time and resources in an organization,” said Rand, who is VP of sales at the creative collaboration platform Ziflow. “But it’s necessary, especially as an organization scales.”

That doesn’t mean a rep should be sitting in frequent multi-hour lectures learning about the product and sales strategy. Instead, it’s about giving a rep room to practice what they learn during onboarding and the freedom to fail without expectations. No matter how experienced a rep is, starting a new job is never easy. 

If you don’t come in with a plan, you risk watching those new hires leave the company and going through the same process again, only a few months later.

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Foster Relationship-Building Opportunities

The first few days of any onboarding program sets the foundation for everything that follows.

Before new hires can start learning about the product or sales process, they need to understand the company’s mission. Why does the product exist? What’s the company’s goal and how does sales fit in that equation? Without answers to those questions, everything that follows can ring hollow, Rand said.

That’s why Rand always brings in the CEO or founder for the first meeting. While a sales leader can share that vision, it’s more meaningful to hear it directly from the founder. They’re often the first salespeople for a company and have the clearest messaging around how to sell the product and why it matters.

“We all want a mission and purpose that’s bigger than ourselves, that’s bigger than the commission check that we might be getting,” Rand said. “If they reflect back on that discussion [with the CEO], it’ll help them connect the dots throughout the training.”   

From there, it’s important to start introducing other team leaders.

Sales reps aren’t going to be working on an island. They need to understand who to reach out to on finance when they’re negotiating a discount, who can help them in product when they need advice on a software integration and who they can count on in marketing for white papers. Introducing other team leaders early on not only helps reps understand the scope of the company and where they fit within it, but it also allows them to establish a natural connection before they need something.

Rand admits this used to be easier in the office when department leaders could pop into onboarding sessions and conversations could naturally strike up around the office. In a remote setting, sales leaders have to be more intentional in building those bonds.

“If somebody goes into a job alone, there’s a risk of losing them very early on if anything goes hard or the job isn’t working out for them ... If they don’t have that bond, they really have no reason to show up at work.”

Since Zoom sessions can be impersonal, Rand recommends creating a game that gets reps to interact one-on-one with the various department team members. In the past, she’s organized a bingo game in which each square is filled with fun facts about different employees across the organization. The new hire then has to reach out to their colleagues and find out if they’re traveled to Alaska or studied in France.

If games aren’t your thing, you can also do a happy hour meet-and-greet. The important thing is to create opportunities for new hires to get ingrained in the company.

The final pillar of support that new hires need to thrive is each other.

The first few months for any new rep are full of rejection and struggles as they find their voice. It can be an isolating experience, especially as they watch veteran peers thrive, said Tom Slocum, program director for RevGenius, a sales networking and training community. Fostering connections early on within the cohort gives new reps a ready-made support group when things get difficult.

“If somebody goes into a job alone, there’s a risk of losing them very early on if anything goes hard or the job isn’t working out for them,” Slocum said. “If they don’t have that bond, they really have no reason to show up at work.”

The best way to build that camaraderie is to pair new reps with each other the first day. Give them time to get to know each other and make them accountable to one another, Slocum said. This gives each new hire a companion throughout the process.

He also suggests mixing reps up in breakout rooms after lectures. Large Zoom meetings can be an intimidating environment to ask questions or process information. Splitting reps up in smaller groups to go over the information makes it more accessible and gets them used to going to each other for support. 

“In breakout rooms I’m encouraging everyone to talk to each other, doing icebreakers or going through challenges together,” Slcoum said. “You want people to feel safe, you want them to feel good and you want them retaining things. And sometimes being in a group of 15 people … it’s not doing much for them.” 

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Break Up Lectures With Hands-On Experience

One of the biggest challenges within any onboarding program is figuring out how to get reps to retain what they’re learning. 

Those first few weeks are chock-full of important information that reps need to succeed, from sales stack tutorials to product demos to strategy sessions. And yet, about half the content reps learn over that period isn’t retained after two months, according to a report from management training firm Sales Readiness Group.   

But it might not just be a retention issue. The hardest part for any salesperson isn’t learning what to say or how to say something (anyone can memorize a pitch), it’s listening to what the customer says and using what they’ve learned to adapt to it.

“Your call can go off track when a customer asks you a question that you don’t know the answer to,” Rand said. “The more prepared you are, the more brain power you’ll have available to answer those tough questions.”  

Lectures don’t give reps that experience, which is why starting practice sessions as early as possible is crucial. 

As the former director of sales and business development for Milestone, an internet marketing company, Slocoum would choose team leads and more experienced sales reps to act as subject matter coaches for the new hires. One team lead might focus on navigating the customer relationship management software, another would tackle objection handling and another might specialize in competitor positioning

“I’m putting you on a team and I want you to feel like you’re part of a family ... If I do it all myself and then throw you in the henhouse with the rest, you’re going to be like, ‘What do I do here?’” 

By the second week, sales reps would sit down with each of those experts to practice what they learned in lecture. The meetings would always start with real experience. For example, the objection handler would have the new hire listen in as they make a series of cold calls. Then, they’d review the objections and run mock scenarios to give the new hire a chance to craft their own responses.

The key is to resist the impulse to correct the new hire the moment they do something wrong, Slocum said. If you wait to correct them at the end, they’re able to experiment with the information you’ve given them and better learn from their mistakes. 

“You want them to take advantage of that hour of training to just let them fail hard and fail fast with no correction,” Slocum said. “At the end, let’s provide feedback. That’s where that practicality and the lab work is coming in and they’re able to retain what they’re seeing.” 

It’s important that you, as a leader, don’t lead every lecture and learning opportunity, Slocum said. Delegate training opportunities to senior leaders on the sales team to lead. When reps work with their peers, they get used to turning to each other for advice. Without that, they’ll struggle to act independently of you as the leader.

“I’m putting you on a team and I want you to feel like you’re part of a family,” Slocum said. “If I do it all myself and then throw you in the henhouse with the rest, you’re going to be like, ‘What do I do here?’” 

Call recordings are also a great resource to give reps practical knowledge. Rand will often walk reps through different exchanges asking them what they heard and what they think will come next. This trains their ear to start asking more complex discovery questions, Rand said. 

Still, reps often learn the most useful information on the sales floor, where they can overhear how a peer tackled a security question or handled a common objection and questions come up naturally. 

“You learn all these tips and tricks through osmosis,” Rand said. “We no longer have that when we’re not in the office.” 

In a remote setting, you have to find a way to replace that experience. Rand suggests creating forums where reps can exchange tips like how they set up their day or respond to a common objection. This could be setting up standing virtual brown bag sessions, creating a hangout room or just empowering leaders on the team to set up their own meetings. 

The more opportunities for reps to learn from each other, the better.

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Set Realistic Goals and Let Your Reps Make Mistakes

Sales leaders often fall into the trap of either spending too much time on training or slapping unrealistic quota expectations on their reps. While practice is good, at some point, reps need to start making calls or they’re never going to learn. 

To do that, you want your reps to feel safe making mistakes with customers and learning from them.

“I believe in failing hard and fast. I’m not talking about burning through your quality inbound leads … I just want them to be comfortable and safe knowing the next 45 days are unmarked for them,” Slocum said. “I want them to just experience everything as fast as possible.” 

The average time it takes a rep to start reaching their full quota is about three months for sales development reps and four months for account executives, according to reports from The Bridge Group, a sales consulting firm. To reach those benchmarks or even exceed them, you need to set realistic goals and ease them into their role. 

Once your reps have all the information they need to start speaking with customers, get them on the phones with low-risk leads, Slocum said. Old contacts, or customers who haven’t spoken with the company in a few months, can be a good source for this. 

They might book a few meetings, but he just wants them to get comfortable speaking with customers. After a week of making calls, he’ll start tailoring training and coaching to help them build up to their quota.

“I just want you to take everything you’ve learned and let me see you put it into practice,” Slocum said. “From there, we can start pulling some levers and making your journey more customizable.” 

Rand suggests building goals around a rep’s weaknesses. So if they’re struggling with product demos, she’ll task them with completing 10 mock demos and three customer demos over the couple weeks. Over time, she’ll layer on other skills to build confidence and the habits they need to succeed.

Each rep’s journey will be different after the first month of training. Some will be great at discovery but struggle with objections. Another might ace email outreach but stumble during demos. Rushing the process with quotas will only derail the rep’s journey, Rand said. 

“[You] need to give time for the person to learn,” Rand said. “In the first few months, reps don’t have a quota because they’re learning. I want them to spend time digging in and learning when they’re not on the phone.”

While their sales may come in fits and starts at the beginning, you’ll end up with a far more productive and consistent team in the long run

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